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https://hdl.handle.net/1822/15962
Título: | Synthesis of new n-ethyl dehydroamino acid derivatives : n-ethyl β,β-dibromo, n-ethyl β-bromo β-substituted, n-ethyl β,β-disubstituted n-protected dehydroamino acid methyl esters |
Autor(es): | Monteiro, Luís S. Andrade, Juliana J. Suárez, Ana C. |
Palavras-chave: | Amino acids Alkylation N-Ethyl dehydroamino acids N-Ethyl β-bromo dehydroamino acids Suzuki cross-coupling Nonnatural amino acids Cross-coupling Protecting groups |
Data: | Nov-2011 |
Editora: | Wiley-VCH Verlag |
Revista: | European Journal of Organic Chemistry |
Resumo(s): | Recently we reported the use of a sequence of alkylation and dehydration methodologies to obtain from the methyl esters of N-(4-nitrophenylsulfonyl)-β-hydroxyamino acids, new non-proteinogenic amino acids, namely, N-ethyl-α,β-dehydroamino acids. Thus, it was possible to obtain for the first time, non-natural amino acids which incorporate both the N-ethyl and α,β-dehydro moieties. Herein, we report the application of this N-alkylation procedure to several methyl esters of β,β-dibromo and β-bromo, β-substituted dehydroamino acids protected with standard amine protecting groups such as tert-butyloxycarbonyl, benzyloxycarbonyl and 4-nitrobenzyloxycarbonyl as well as acyl and sulfonyl groups. The procedure allows the synthesis of the methyl esters of N-protected, N-ethyl, β,β-dibromo and N-ethyl, β-bromo, β-substituted dehydroamino acids in fair to high yields. Some of these N-ethylated dehydroamino acid derivatives were used as substrates in cross coupling reactions to give N-ethyl, β,β-disubstituted dehydroalanine derivatives. |
Tipo: | Artigo |
URI: | https://hdl.handle.net/1822/15962 |
DOI: | 10.1002/ejoc.201100907 |
ISSN: | 1434-193X |
Arbitragem científica: | yes |
Acesso: | Acesso aberto |
Aparece nas coleções: | CDQuim - Artigos (Papers) |
Ficheiros deste registo:
Ficheiro | Descrição | Tamanho | Formato | |
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2011-Eur. J. Org. Chem I.pdf | 259,56 kB | Adobe PDF | Ver/Abrir |